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Enantioselective Iridium-Catalyzed Allylic Amination of Ammonia and Convenient Ammonia Surrogates

Mark J. Pouy, Andreas Leitner, Daniel J. Weix, Satoshi Ueno and John F. Hartwig*

*Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801, Email: jhartwiguiuc.edu

M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig, Org. Lett., 2007, 9, 3949-3952.

DOI: 10.1021/ol701562p (free Supporting Information)


Abstract

Iridium-catalyzed allylation of potassium trifluoroacetamide or the highly reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms a range of conveniently protected, primary, α-branched allylic amines in high yields, high branched-to-linear regioselectivities, and high enantiomeric excess.

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Direct, Intermolecular, Enantioselective, Iridium-Catalyzed Allylation of Carbamates to Form Carbamate-Protected, Branched Allylic Amines

D. J. Weix, D. Markovi, M. Ueda, J. F. Hartwig, Org. Lett., 2009, 11, 2944-2947.

Regio- and Enantioselective Allylic Amination of Achiral Allylic Esters Catalyzed by an Iridium-Phosphoramidite Complex

T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 15164-15165.


Key Words

Protected Primary Amines, Allylic Amines, Amides, Carbamates


ID: J54-Y2007-3070